The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Cornelia Hojnik; Anne Mueller; Tobias Gloe; Thisbe Lindhorst; Tanja Wrodnigg

doi:10.1002/ejoc.201600458

The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Cornelia Hojnik, Anne Mueller, Tobias Gloe, Thisbe Lindhorst^*, Tanja Wrodnigg^*

^*Korrespondierende/r Autor/-in für diese Arbeit

Institut für Organische Chemie (6410)

Publikation: Beitrag in einer Fachzeitschrift › Artikel › Begutachtung

Abstract

The Amadori rearrangement was investigated for the synthesis of C-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-natural C-glycosyl-type glycoconjugates of the d-gluco and d-manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.

Originalsprache	englisch
Seiten (von - bis)	4328-4337
Fachzeitschrift	European Journal of Organic Chemistry
Jahrgang	2016
Ausgabenummer	25
DOIs	https://doi.org/10.1002/ejoc.201600458
Publikationsstatus	Veröffentlicht - 2016

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Human- & Biotechnology

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10.1002/ejoc.201600458Lizenz: CC BY 4.0

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abstract = "The Amadori rearrangement was investigated for the synthesis of C-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-natural C-glycosyl-type glycoconjugates of the d-gluco and d-manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.",

author = "Cornelia Hojnik and Anne Mueller and Tobias Gloe and Thisbe Lindhorst and Tanja Wrodnigg",

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AB - The Amadori rearrangement was investigated for the synthesis of C-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-natural C-glycosyl-type glycoconjugates of the d-gluco and d-manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.

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M3 - Article

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The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

Abstract

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